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Chatham Luxury Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
682 rentals in Chatham.
Pleasant Forest Shores cottages #4 : So. Chatham, holiday rental in Chatham
Pleasant Forest Shores cottages #4 : So. Chatham, holiday rental in Chatham
Pleasant Forest Shores cottages #4 : So. Chatham, holiday rental in Chatham

Pleasant Forest Shores cottages #4 : So. Chatham

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful home near Jacknife Beach and bike trail, holiday rental in Chatham
Beautiful home near Jacknife Beach and bike trail, holiday rental in Chatham
Beautiful home near Jacknife Beach and bike trail, holiday rental in Chatham

Beautiful home near Jacknife Beach and bike trail

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Convenient to all amenities and beaches in Chatham, holiday rental in Chatham
Convenient to all amenities and beaches in Chatham, holiday rental in Chatham
Convenient to all amenities and beaches in Chatham, holiday rental in Chatham

Convenient to all amenities and beaches in Chatham

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach, holiday rental in Chatham
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach, holiday rental in Chatham
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach, holiday rental in Chatham

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Fully Updated Chatham Cottage Near Hardings Beach, holiday rental in Chatham
Fully Updated Chatham Cottage Near Hardings Beach, holiday rental in Chatham
Fully Updated Chatham Cottage Near Hardings Beach, holiday rental in Chatham

Fully Updated Chatham Cottage Near Hardings Beach

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming 3b/2ba House Close to Downtown/Pier/Beach, holiday rental in Chatham
Charming 3b/2ba House Close to Downtown/Pier/Beach, holiday rental in Chatham
Charming 3b/2ba House Close to Downtown/Pier/Beach, holiday rental in Chatham

Charming 3b/2ba House Close to Downtown/Pier/Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Renovated cottage 1 mile to beach in Chatham!, holiday rental in Chatham
Renovated cottage 1 mile to beach in Chatham!, holiday rental in Chatham
Renovated cottage 1 mile to beach in Chatham!, holiday rental in Chatham

Renovated cottage 1 mile to beach in Chatham!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Outermost Waterfront Chatham Home w/ Wraparound Views, holiday rental in Chatham
Outermost Waterfront Chatham Home w/ Wraparound Views, holiday rental in Chatham
Outermost Waterfront Chatham Home w/ Wraparound Views, holiday rental in Chatham

Outermost Waterfront Chatham Home w/ Wraparound Views

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches, holiday rental in Chatham
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches, holiday rental in Chatham
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches, holiday rental in Chatham

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Chatham Walk to Beach Cape Cod, holiday rental in Chatham
Chatham Walk to Beach Cape Cod, holiday rental in Chatham
Chatham Walk to Beach Cape Cod, holiday rental in Chatham

Chatham Walk to Beach Cape Cod

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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4 Bedrooms, 2 Baths, Sleeps 8, holiday rental in Chatham
4 Bedrooms, 2 Baths, Sleeps 8, holiday rental in Chatham
4 Bedrooms, 2 Baths, Sleeps 8, holiday rental in Chatham

4 Bedrooms, 2 Baths, Sleeps 8

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Discounted Summer prices! Book now! WATERVIEWS! 4min drive to Hardings Beach!, holiday rental in Chatham
Discounted Summer prices! Book now! WATERVIEWS! 4min drive to Hardings Beach!, holiday rental in Chatham
Discounted Summer prices! Book now! WATERVIEWS! 4min drive to Hardings Beach!, holiday rental in Chatham

Discounted Summer prices! Book now! WATERVIEWS! 4min drive to Hardings Beach!

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Chatham Cape Cod Vacation Rental (15578), holiday rental in Chatham
Chatham Cape Cod Vacation Rental (15578), holiday rental in Chatham
Chatham Cape Cod Vacation Rental (15578), holiday rental in Chatham

Chatham Cape Cod Vacation Rental (15578)

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Clean, Bright, and Spacious; Family Friendly!, holiday rental in Chatham
Clean, Bright, and Spacious; Family Friendly!, holiday rental in Chatham
Clean, Bright, and Spacious; Family Friendly!, holiday rental in Chatham

Clean, Bright, and Spacious; Family Friendly!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach, holiday rental in Chatham
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach, holiday rental in Chatham
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach, holiday rental in Chatham

New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Seaside condo with patio, beach access, loft, board games, gas grill, & firepit, holiday rental in Chatham
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit, holiday rental in Chatham
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit, holiday rental in Chatham

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!, holiday rental in Chatham
Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!, holiday rental in Chatham
Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!, holiday rental in Chatham

Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Luxurious Home with Pool & Game Room in Cape Cod, holiday rental in Chatham
Luxurious Home with Pool & Game Room in Cape Cod, holiday rental in Chatham
Luxurious Home with Pool & Game Room in Cape Cod, holiday rental in Chatham

Luxurious Home with Pool & Game Room in Cape Cod

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C, holiday rental in Chatham
Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C, holiday rental in Chatham
Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C, holiday rental in Chatham

Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor, holiday rental in Chatham
SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor, holiday rental in Chatham
SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor, holiday rental in Chatham

SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Renovated, modern Chatham beach house with lots of cozy charm, holiday rental in Chatham
Renovated, modern Chatham beach house with lots of cozy charm, holiday rental in Chatham
Renovated, modern Chatham beach house with lots of cozy charm, holiday rental in Chatham

Renovated, modern Chatham beach house with lots of cozy charm

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Harwich home with private pool in great location!, holiday rental in Chatham
Beautiful Harwich home with private pool in great location!, holiday rental in Chatham
Beautiful Harwich home with private pool in great location!, holiday rental in Chatham

Beautiful Harwich home with private pool in great location!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Classic Cape House Walking Distance to the Beach, holiday rental in Chatham
Classic Cape House Walking Distance to the Beach, holiday rental in Chatham
Classic Cape House Walking Distance to the Beach, holiday rental in Chatham

Classic Cape House Walking Distance to the Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Steps to Chatham Center & Lighthouse Beach - charming home with central AC, holiday rental in Chatham
Steps to Chatham Center & Lighthouse Beach - charming home with central AC, holiday rental in Chatham
Steps to Chatham Center & Lighthouse Beach - charming home with central AC, holiday rental in Chatham

Steps to Chatham Center & Lighthouse Beach - charming home with central AC

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more..., holiday rental in Chatham
5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more..., holiday rental in Chatham
5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more..., holiday rental in Chatham

5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more...

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views, holiday rental in Chatham
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views, holiday rental in Chatham
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views, holiday rental in Chatham

Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Chatham Cape Cod Vacation Rental (16729), holiday rental in Chatham
Chatham Cape Cod Vacation Rental (16729), holiday rental in Chatham
Chatham Cape Cod Vacation Rental (16729), holiday rental in Chatham

Chatham Cape Cod Vacation Rental (16729)

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Harwich Retreat, Private Pool, Beach nearby, Family Home, holiday rental in Chatham
Harwich Retreat, Private Pool, Beach nearby, Family Home, holiday rental in Chatham
Harwich Retreat, Private Pool, Beach nearby, Family Home, holiday rental in Chatham

Harwich Retreat, Private Pool, Beach nearby, Family Home

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Chatham Cape Cod Vacation Rental (15639), holiday rental in Chatham
Chatham Cape Cod Vacation Rental (15639), holiday rental in Chatham
Chatham Cape Cod Vacation Rental (15639), holiday rental in Chatham

Chatham Cape Cod Vacation Rental (15639)

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chatham Cape Cod Waterfront Vacation Rental (12273), holiday rental in Chatham
Chatham Cape Cod Waterfront Vacation Rental (12273), holiday rental in Chatham
Chatham Cape Cod Waterfront Vacation Rental (12273), holiday rental in Chatham

Chatham Cape Cod Waterfront Vacation Rental (12273)

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Walk to Ridgevale Beach From Family Friendly Home, holiday rental in Chatham
Walk to Ridgevale Beach From Family Friendly Home, holiday rental in Chatham
Walk to Ridgevale Beach From Family Friendly Home, holiday rental in Chatham

Walk to Ridgevale Beach From Family Friendly Home

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Carriage House with Beautiful Water View, Steps to Beach & Main Street, holiday rental in Chatham
Carriage House with Beautiful Water View, Steps to Beach & Main Street, holiday rental in Chatham
Carriage House with Beautiful Water View, Steps to Beach & Main Street, holiday rental in Chatham

Carriage House with Beautiful Water View, Steps to Beach & Main Street

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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5 Star Waterfront in North Chatham with dock, fire pit, and beach, holiday rental in Chatham
5 Star Waterfront in North Chatham with dock, fire pit, and beach, holiday rental in Chatham
5 Star Waterfront in North Chatham with dock, fire pit, and beach, holiday rental in Chatham

5 Star Waterfront in North Chatham with dock, fire pit, and beach

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lovely Stage Harbor Estate Guest House W/Private Beach to Use, holiday rental in Chatham
Lovely Stage Harbor Estate Guest House W/Private Beach to Use, holiday rental in Chatham
Lovely Stage Harbor Estate Guest House W/Private Beach to Use, holiday rental in Chatham

Lovely Stage Harbor Estate Guest House W/Private Beach to Use

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Lovely cottage near beach and town - screened porch, outdoor shower, picnic area, holiday rental in Chatham
Lovely cottage near beach and town - screened porch, outdoor shower, picnic area, holiday rental in Chatham
Lovely cottage near beach and town - screened porch, outdoor shower, picnic area, holiday rental in Chatham

Lovely cottage near beach and town - screened porch, outdoor shower, picnic area

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy Cape near Chatham Center, holiday rental in Chatham
Cozy Cape near Chatham Center, holiday rental in Chatham
Cozy Cape near Chatham Center, holiday rental in Chatham

Cozy Cape near Chatham Center

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!, holiday rental in Chatham
PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!, holiday rental in Chatham
PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!, holiday rental in Chatham

PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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South Chatham Cape Cod Vacation Rental (50), holiday rental in Chatham
South Chatham Cape Cod Vacation Rental (50), holiday rental in Chatham
South Chatham Cape Cod Vacation Rental (50), holiday rental in Chatham

South Chatham Cape Cod Vacation Rental (50)

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6., holiday rental in Chatham
Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6., holiday rental in Chatham
Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6., holiday rental in Chatham

Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street, holiday rental in Chatham
Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street, holiday rental in Chatham
Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street, holiday rental in Chatham

Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, holiday rental in Chatham
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, holiday rental in Chatham
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, holiday rental in Chatham

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Full Renovation! Amazing Spot with Views!, holiday rental in Chatham
Full Renovation! Amazing Spot with Views!, holiday rental in Chatham
Full Renovation! Amazing Spot with Views!, holiday rental in Chatham

Full Renovation! Amazing Spot with Views!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Chatham 3 Bedroom/2 Bath Retreat, holiday rental in Chatham
Chatham 3 Bedroom/2 Bath Retreat, holiday rental in Chatham
Chatham 3 Bedroom/2 Bath Retreat, holiday rental in Chatham

Chatham 3 Bedroom/2 Bath Retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches, holiday rental in Chatham
Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches, holiday rental in Chatham
Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches, holiday rental in Chatham

Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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South Chatham Cape Cod Vacation Rental (14295), holiday rental in Chatham
South Chatham Cape Cod Vacation Rental (14295), holiday rental in Chatham
South Chatham Cape Cod Vacation Rental (14295), holiday rental in Chatham

South Chatham Cape Cod Vacation Rental (14295)

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN, holiday rental in Chatham
OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN, holiday rental in Chatham
OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN, holiday rental in Chatham

OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Relaxing, peaceful area close to beaches, downtown Chatham, and walking trails., holiday rental in Chatham
Relaxing, peaceful area close to beaches, downtown Chatham, and walking trails., holiday rental in Chatham
Relaxing, peaceful area close to beaches, downtown Chatham, and walking trails., holiday rental in Chatham

Relaxing, peaceful area close to beaches, downtown Chatham, and walking trails.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Newly Renovated Cape House .9Miles from the Beach, holiday rental in Chatham
Newly Renovated Cape House .9Miles from the Beach, holiday rental in Chatham
Newly Renovated Cape House .9Miles from the Beach, holiday rental in Chatham

Newly Renovated Cape House .9Miles from the Beach

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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WALK TO RESTAURANTS, SHOPS & LIQUOR STORE- CLOSE TO DOWNTOWN CHATHAM!!!, holiday rental in Chatham
WALK TO RESTAURANTS, SHOPS & LIQUOR STORE- CLOSE TO DOWNTOWN CHATHAM!!!, holiday rental in Chatham
WALK TO RESTAURANTS, SHOPS & LIQUOR STORE- CLOSE TO DOWNTOWN CHATHAM!!!, holiday rental in Chatham

WALK TO RESTAURANTS, SHOPS & LIQUOR STORE- CLOSE TO DOWNTOWN CHATHAM!!!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Chatham Break! 3BR, large quiet yard, walk to shops + restaurants., holiday rental in Chatham
Chatham Break! 3BR, large quiet yard, walk to shops + restaurants., holiday rental in Chatham
Chatham Break! 3BR, large quiet yard, walk to shops + restaurants., holiday rental in Chatham

Chatham Break! 3BR, large quiet yard, walk to shops + restaurants.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 682